When Should You Sleep With Him?

Not long ago, hoping to silence my moaning about a particularly rough dating drought, a girlfriend volunteered to fix me up with her old friend T. One e-mail from him and I was smitten. After a day of message volleying, we agreed to talk on the phone that night.

T. sounded as charming as he was online. I wanted to speed things along—finally I'd found someone worthy of my attention—and I suggested we meet right that minute. He agreed and rushed over to my apartment. From then on we were coupled up, quite literally, since we spent most of our time horizontal in his place or mine.

Soon enough, though, the mornings after brought a sinking "this isn't going to work" feeling. Charmingly boyish now seemed plain immature, and enthusiastic was more like hyper. The more time we spent vertical, actually talking, the less I liked him. So one night, during a romantic dinner at my favorite Italian bistro (I'd insisted that we finally go somewhere other than our apartments), I announced, "I don't think we have what it takes to make it in the long run." After six months of ordering takeout and sleeping over, we were breaking up on our first real date.

This wasn't the only time I'd fast-forwarded to the sex. In fact, I'd spent a good deal of my romantic life doing what I can only call dating in bed. But I couldn't help what-iffing: What if that first night, I'd hung up the phone and gone to sleep (alone and, yes, a little horny, but giddy about what might happen)? I might have discovered over the course of a few conversations that I wasn't interested. Instead, I lost a lot of time, and T. felt he'd lost more than that. I'm not bragging, but he took our breakup hard. Maybe if I'd practiced a little sexual restraint I would have saved myself a lot of confusion and him some hurt.

In the post-Sex and the City era we live in, any hand-wringing over a question as old-fashioned as "Did I have sex with him too soon?" sounds like a teen movie or, worse, the book The Rules. But I'm definitely not a Rules girl. I reject game playing, refuse to subscribe to the not-before-the-third-date law and believe women are in charge of their sex lives the same way men are. Still, the T. episode left me in need of advice on the issue, so I asked around.

"Having sex too soon is the biggest mistake I see women making," says Nina Atwood, a Dallas-based therapist who is the author of Temptations of the Single Girl and the voice of reason on singlescoach.com. "We always tout the exception: A woman sleeps with a guy on the first date, and they wind up married and it's all great. But for every one of those fairy tales, I've heard 150 stories from women who've started down that road and didn't end up in the loving relationship they wanted."

Asking yourself whether you're having sex too soon, Atwood hastens to point out, doesn't mean catapulting back to the days when women weren't entitled to be as freely, truly, madly and deeply sexual as men. "It's about too soon' for your own well-being and happiness," she says, "not too soon' in the eyes of the world." Laura Berman, Ph.D., author of Real Sex for Real Women, also believes that waiting allows us to avoid what she calls "emotional shrapnel" but adds that "anytime you're putting too' on your sex life—too much, too little, too soon—it shouldn't come from a place of pressure and expectation."

So block out what anyone else thinks, and come up with the sexual timing that works best for you. But while you're at it, consider the following five reasons to hold off a little: They come from therapists, sexologists and real women, and they're extremely compelling.

Because You'll Have Better Sex

Christien, 31, says that after waiting six months to sleep with her boyfriend, closing the deal was "intense—in a good way." She decided to wait, she says, because "he showed looks like it can go somewhere' potential" and she "could establish a bond with him—both for romance and friendship." But waiting hasn't always been Christien's thing. She'd often slept with guys right away, and the experiences proved to be so-so because "there wasn't that feeling of togetherness."

Bonding has awesome benefits, says Laura Berman: "Research shows that the number-one component of women's sexual satisfaction is not orgasm; it's connection to the person they're with." The more connected you feel, the better the sex will be.

For Christien, this closeness makes for amazing sex because she allows herself to offer and enjoy a full-course experience that includes kissing and oral sex. "I feel more sensual. I don't worry about how my body looks. I already know he's really attracted to me and desires me. I can be relaxed, funny, awkward, all of it—my most comfortable, sexiest self."

What about those women who get busy right away because sex is a part of their mate-appraisal process? (They prefer to know sooner rather than later if the goods are, well, good.) The problem with that logic, says Logan Levkoff, Ph.D., sexologist and author of Third Base Ain't What It Used to Be, is that the first time isn't always representative of what sex will be like: "It can get better as people learn about each other's bodies and speak up about their needs."

Because You Won't Confuse Chemistry With Compatibility

Sometimes you meet a guy and the vibe is so hot you know the sex will be too. Why not just go for it right then? Because heat and hormones can be mistaken for true affinity, says Atwood. "Look ahead and think, OK, this feels wonderful, but where will we be tomorrow or the next day?"

That's asking for an awful lot of self-discipline, though, at the very moment when our judgment may be impaired by powerful brain chemicals. Sexual arousal triggers surges of the feel-good neurotransmitter dopamine and the hormone oxytocin, which stimulates feelings of attachment and love. Surely this chemical cascade was at work when T. and I got together. How does a woman on the threshold of passion manage to put mind over mojo?

Jennifer R. Berman, M.D., Laura's sister and codirector of the Female Sexual Medicine Center at UCLA, suggests a practical technique for avoiding impulsive decisions: "In the midst of a potentially risky situation, develop a habit of asking yourself, Do I care if this guy never calls me again?' Then stop, think, choose and think again."

Because You'll Do It for the Right Reasons

What might constitute a wrong reason to sleep with someone? Levkoff names some that she frequently hears: to keep him interested; to be publicly recognized as "in a relationship"; out of habit; because you need a man (any man) to validate your attractiveness. These are motives we don't always admit to ourselves, she says. But understanding the deeper reasons we might be jumping into bed too soon can head off unhappy endings.

Here's where it gets a little psychoanalytic: You might need to trace your sexual story line back to its beginning to figure out what drives your decisions. Mine starts, "Once upon a time, a girl who lacked self-confidence sought male affirmation, and at 15 she impulsively lost her virginity to a guy whom she'd just met and whose name she can no longer remember…." Despite growing older (and, presumably, wiser), I haven't strayed far from that script. My first encounter set in motion a cycle that undermined my evolving relationship needs. Since I was no longer a 15-year-old who needed sex to demonstrate my desirability or feel better about myself, my pattern wasn't terribly satisfying anymore. "Many women act based on who they were rather than who they are now," says New Jersey-based life coach and counselor Jeree Wade. For those like me who would benefit from replacing an outdated sex-life script, Wade advises delaying gratification, a practice she believes is the hallmark of "making sexual decisions that are good for you." The longer you wait, the more information you can gather about a new relationship—how you really feel about him, how he feels about you—the less likely you are to reflexively reenact a past scenario.

Because Sex Is the Big Deal You Think It's Not

We're talking about an activity that can sometimes lead to irreversible consequences: an STD, a child, life-changing drama (betrayal, restraining orders, etc.). "Sex is this very heavy thing that everyone does their best to make light of," says Dorothy Robinson, coauthor of the morbidly titled Dating Makes You Want to Die. But, she warns, the heaviness can catch up with you by the time you wake up the next morning.

For Lynn, 31, second-date sex led to a third date (and then some). Soon she was falling hard for the guy, but it turned out he wasn't exactly on the same page. When he moved to Texas with barely a goodbye, a confused Lynn wondered, What about us? and felt jilted. "It was as if the last few months were one big misunderstanding," she says. "To him, our relationship was the dumpable kind; for me it was a keeper."

Atwood says it's a pattern she sees with many couples. When we rush into bed, she observes, the chances are greater that we find ourselves wanting the man either more, or less, than he wants us. In either case, we're off balance instead of being in that relationship comfort zone where both parties desire each other in roughly the same way and to the same degree. The longer you wait, Atwood says, the clearer your sense of where you stand with him is, which helps you decide what you want to do next. Hey, maybe you'll go for the sex anyway, but you'll both know better what lopsided thing you could be getting into.

Because Sex Right Away Can Make You Feel Empowered—But It Can Also Make You a Needy Mess

Catherine, 29, typically thinks long and hard about a guy's husband-material quotient before sleeping with him. But a few months after splitting with her boyfriend of three years, she decided to take a break from serious relationships. "I met a man, he was hot and I went for it," she says. And though she didn't start off with lofty expectations, once they had sex, she suddenly wanted more: "I didn't even like him that much, but I wanted him to like me that much."

True sexual empowerment, Levkoff believes, "is about knowing who you are and knowing what you need to be fulfilled emotionally and physically." And sometimes, for some women, that may mean making the tough decision to say, "I need to be intimate before I have sex."

If, after reading this, you're all, "Uh-oh, we've already gotten it on too early! Have I flubbed any chance for a long-lasting connection?" Nina Atwood has excellent do-over advice to chart a less sexually charged course: The next time he calls and wants to get together, suggest going out to dinner or for coffee—someplace where clothes must stay on. Start by telling him you're very interested in him and you want to see where this can go, but you made the mistake of having sex too soon.

"Open up a dialogue, saying something like, You won't hurt my feelings if you don't feel the same, but I want to see if we have couple potential,'" Atwood advises. "You don't have to stop sleeping with him, but you need to find out where you stand." For anyone who thinks this script seems heavy for morning-after chitchat, Atwood offers a sobering response: "I find it ironic that people would rather have sex than discuss the ramifications of it."

"Delay gratification" and "Stop, think, choose, think again"—the expert advice suggests this bottom line: Wait. Not forever. Perhaps just one date or even one minute more, until you're sure this guy and this situation make sense for you. Because sometimes knowing what you want feels as good as sex—maybe even better.